(2H-1,3-benzodioxol-5-yl)boronic acid → HCID 57863157, compound

HRID 2426285Notes

Reaction equation

HRID 2426285 reaction equation
Cl[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([N+:12]([O-:14])=[O:13])[CH:8]=2)[N:3]=1.B(O)(O)[C:16]1[CH:21]=[CH:20][C:19]2[O:22][CH2:23][O:24][C:18]=2[CH:17]=1.O.O.O.O.O.O.O.O.[OH-].[Ba+2].[OH-]>C1COCC1.[Pd](Cl)Cl>[O:22]1[C:19]2[CH:20]=[CH:21][C:16]([C:2]3[CH:11]=[CH:10][C:9]4[C:4](=[CH:5][CH:6]=[C:7]([N+:12]([O-:14])=[O:13])[CH:8]=4)[N:3]=3)=[CH:17][C:18]=2[O:24][CH2:23]1

Participants

6

Reactant 3

HCID 2734371(2H-1,3-benzodioxol-5-yl)boronic acidHCID 109217232-Chloro-6-nitroquinolineHCID 17749109Barium hydroxide, octahydrate

Product 1

HCID 57863157HCID 57863157, compoundYield 27.2%

Reagents, catalysts & solvents 2

HCID 24290Palladium ChlorideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

2-chloro-6-nitroquinoline (5.2 g, 25 mmol) (prepared according to Byoung S. L. et al. Heterocycles. 1998, 48.12, 65), 3,4-(methylenedioxy)phenylboronic acid (5.0 g, 30 mmol), palladium dichloride bis(triphenilphosphine) (350 mg, 0.5 mmol) and barium hydroxide octahydrate (18.9 g, 60 mmol) in 150 ml of anhydrous THF are stirred at 65° C. for 20 hours. The mixture of reaction is evaporated under vacuum and the residue is chromatographed on silica gel (CH2Cl2) to afford 2.0 g (27%) of the titled product.

Workup

  1. additionThe mixture of reaction
  2. customis evaporated under vacuum
  3. customthe residue is chromatographed on silica gel (CH2Cl2)

Sources & evidence

ORD record
ord-459249bb05194f7ea2871188b2f38bfd
Source dataset
uspto-grants-2011_06
Patent number
US07968558B2

Reaction notes

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